What Chatbots Can Learn from Pickup Artists

Social engineering in the age of conversational UI can learn from Neil Strauss’ “The Game”

I believe messaging platforms are the new dashboard (or desktop) for people.

Wired’s Chris Anderson famously wrote in 2010 that apps were already changing the way we utilize the web. We went from desktop computers to cell phones with apps quickly, but now something like 70% of people use Facebook Messenger every day, so the next frontier for brands and startups to conquer is messaging platforms. Startups (like BarkBox), content providers and services are launching conversational initiatives where they send content to people exclusively on these platforms with great success. At BarkBoxwe rely heavily on this and interact with roughly 25% of our customers every month via SMS, messenger or chat. In this way we drive engagement with our customers, increase sales, product develop and provide service.

What we are discovering is that there is not a lot of advanced UX thinking or interface terminology at all with regards to conversational UI. It’s very two dimensional as far as how it was built, leading to very basic interaction models between users and customer service or bots. You ask a question. You get an answer back. How can we make that experience better and create a rapport…build in less friction and more empathy with conversational UI? We would like to turn it into an experience. It’s a bit of a curve ball, but I think we can learn a lot from pickup artists.

Back before I was married, I read that book “The Game” by Neil Strauss. It was written in 2005 and caused a fair bit of controversy. Neil was a Rolling Stone reporter who immersed himself in an entire world of pickup art. He went from being a nerdy writer, to become someone who used social engineering to befriend and successfully flirt with women. Some of the techniques are are morally questionable, however, they did highlight a systematic approach to arhiteting conversations with people you don’t know. Here are a few interesting things that pickup artists do that conversational UI designers can learn from:

The opener After walking into a group of strangers, pickup artists immediately find something interesting enough to most of them to start a dialogue. They are programmed with ‘openers’. Takeaway: AI bots don’t have an icebreaker. No emotional way of engaging in the early part of the conversation.

The Hook I think part of the reason for the title of Strauss’ book is that pickup artists have identified routines. A routine in this instance is a script for how to deal with specific situation and deploy empathy to create rapport. For a pickup artist, it may be as simple as changing focus on the conversation from a female target, to their male colleagues — or initiating a more interesting conversation rather than just offering a drink. Takeaway: In a conversational UI, if a user is changing a password, you can create better experience by creating a narrative (beginning, middle, end) and if our chatbot knows this, it can inject some scripted humor in the middle. “Good things dogs don’t write the passwords, since computer keyboards never respond well to paws!”

The Exhange The Exchange is simultaneous focus on different outcomes. A pickup artist knows about different outcomes (and more importantly, is willing to accept them) before they ask for a number or a date. Leaving someone after you have engaged them in an emotional way is usually the best way to get them to come back. Takeaway: The bot should know “Hey it seems like you’re not really sure about this purchase yet, is it cool if I contact you again in two or three weeks?”

The Context Pickup artists have learned a trick where a target will respond favorably if they think they already have a shared history and narrative. Meaning, they will try to move locales if they already initiated a conversation at a first bar or club. Takeway: We need to get the know the users — even if they engage with us on various platforms. If a user comment on your Instagram — you should know that when chatting with the user later on twitter.

In summary, remember the following things when working in conversational UI:

What is an engaging way to start a conversation? What is your icebreaker? This will be different depending on industry. A conversation initiated to reset a password is a lot different from one where a dog owner is trying to get ideas about gifts for their dog’s personality.

Remember an chatbot needs a narrative. Beginning, middle, and end. We are looking into different routines that can be reused — depending on scenario and user. This is The Game. The more routines we process, the better we become at finding what works in different scenarios and how to become more engaging. We’d also hope to be able to identify early if the human on the other end is short for time, and not looking for humor. Like code modules, our bots or service staff can become better if we test and improve on our routines for different user types. We also know from studying routines things like it’s best to offer a discount or sale at the beginning of a conversation. We’ve found that if you inject an offer toward the end, the customer feels like it discredits the entire exchange.

A pickup artist’s favorite way to end a conversation is what they call “The Close.” There is the phone number close, and the kiss. BUT, there are objectives along the way that can be met, such as an informal agreement to going out on another date. In the same way pickup artists utilize what I’m calling above “The Give”, a chatbot needs to have multiple outcomes that are acceptable, not just going straight for a sale.

Finally, we need to utilize social engineering tools to create rapport but with respect for the user. Referencing memory points in the past will create a stronger bond in the present. There are many tools to create a better experience for the user, but at the end of the day we need to keep in mind that we are serving them. Conversational UI can be amazing to create entertaining and engaging dialog with users and by being more analytical about our approach to this relationship we can create amazing experiences. However, as with any relationship, we should be mindful that that morality needs to play an essential part for checks and balances. You don’t want to sell someone a product that they don’t need or be that annoying person who text way too many time…